Synthesis of [3.3.1] Bicyclic Compounds by a Brønsted Acid Catalysed Double Intramolecular Michael Addition | Zendy

Mendoza Abraham | Zendy; Pardo Pilar | Zendy; Rodríguez Félix | Zendy; Fañanás Francisco J. | Zendy

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Synthesis of [3.3.1] Bicyclic Compounds by a Brønsted Acid Catalysed Double Intramolecular Michael Addition

Author(s) -

Mendoza Abraham,

Pardo Pilar,

Rodríguez Félix,

Fañanás Francisco J.

Publication year - 2010

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201001109

Subject(s) - bicyclic molecule , intramolecular force , michael reaction , brønsted–lowry acid–base theory , chemistry , intramolecular reaction , stereochemistry , catalysis , organic chemistry , medicinal chemistry

Cyclisation sequence : An efficient method for the synthesis of [3.3.1] bicyclic compounds from easily available ynone derivatives has been developed. The reaction is based on an unprecedented double intramolecular Michael addition (DIMA) of an oxygen‐centred and a carbon‐centred nucleophile to the ynone (see scheme).

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